


someday.

by ruzekhalstead



Series: halstead & upton one-shots. [8]
Category: Chicago Fire, Chicago Med, Chicago PD (TV)
Genre: Chicago Med - Freeform, Chicago PD - Freeform, F/M, Jealous Hailey, Molly's (Chicago Fire), One Chicago (Chicago Franchise), Upstead
Language: English
Status: Completed
Published: 2020-04-23
Updated: 2020-04-23
Packaged: 2021-03-02 01:54:43
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,211
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23797255
Author URL: https://archiveofourown.org/users/ruzekhalstead/pseuds/ruzekhalstead
Summary: “plus, why would he get back together with erin when he’s clearly in love with you?”-prompt: erin is back in town and asks jay out for drinks. hailey isn't sure how to feel about it and finds herself at molly's, throwing back shots with will halstead (he totally ships upstead).
Relationships: Jay Halstead & Hailey Upton, Jay Halstead & Will Halstead, Jay Halstead/Hailey Upton, Will Halstead & Hailey Upton
Series: halstead & upton one-shots. [8]
Series URL: https://archiveofourown.org/series/1634428
Comments: 11
Kudos: 94





	someday.

the team is all at their desks, catching up on paperwork when jay’s phone starts ringing.

he glances at it quickly, almost as if he plans on letting it go to voicemail, but then doubles back as his eyes widen. he hesitates to grab it, but ultimately decides he probably should. so, he grabs his phone and quietly ducks out to the break room.

hailey is watching, because of course she is. she happens to look up as his phone starts ringing, just in case it was hers, and catches his reaction. he isn’t very subtle about it, but he probably isn’t thinking people are watching him either. he spends a few minutes in the break room and hailey would be lying if she said she isn’t glancing at the door every few seconds.

her curiosity is starting to get the best of her, so she grabs her near empty coffee mug and subtly enters the break room.

when she enters, jay is sitting at the table. his phone is on the table and his chin is in his hands; his eyes are blank and he’s staring off into space.

“hey, you alright?” she questions as she fills her mug up with fresh coffee. she tries to act nonchalant, like she isn’t dying to know.

jay doesn’t reply.

hailey raises an eyebrow and sits down across from him at the table; his eyes don’t flit to her.

“jay?”

his light eyes finally lift to glance at her and he looks confused, and slightly desperate. “that was erin on the phone.”

there are things hailey expects to hear on the daily; even extremely off things, given what they do for a living. however, this is definitely not one of those things.

she chokes on a sip of her coffee and curses when it dribbles down her chin. “i’m sorry, what?”

jay allows himself to chuckle, watching as she licks her lips free of coffee. she’s glad she can still provide him some amusement. “erin. she’s in town and wants to see me.”

“oh,” it’s the only thing hailey can say because she doesn’t want to overstep; jay raises an eyebrow. “sorry, i'm just surprised is all.”

jay runs a frustrated hand through his hair. “you're telling me,” he mumbles in response. “what should i do?”

hailey's eyes widen; she isn’t expecting him to ask her that. “well, you have to go, right?” she replies, “i mean, she clearly wants to see you.”

jay's facial expression stays blank. “right…”

the passivity on jay's face starts to make hailey nervous; she can’t read his expression and has no idea what he’s thinking. so, she starts to babble.

“maybe she has something important to tell you, like maybe she’s pregnant,” jay's eyes snap to look at her and hailey blanches. “not with you, obviously.” jay is still staring at her and she cringes; she’s absolutely butchering this conversation. “or maybe she wants to get back together.”

somehow, hailey’s brain has not connected to her vocal cords and she still continues to speak.

hailey frowns; by saying that, it’s put unwelcome thoughts in her own mind, and she doesn’t like it. she doesn’t want to picture jay and erin back together; why the hell would she even mention it?

jay is clearly confused as well; he’s finally showing some emotion, as he can’t fathom why hailey would say such awkward things. but she looks uncomfortable and she refuses to make eye contact and she’s inching out of her seat, as if preparing to make a run for it. so, he doesn’t press.

“i guess i’ll just have to meet her to find out.”

hailey hates that answer. she hates it because now she’s planted the seed of a relationship in his brain and she knows as soon as he sees his former flame, he’ll go all heart eyes and that will be that. she hates it.

“hey hails,” her attention lands on her new roommate, who’s peeking her head in the doorway with a gentle smile, “i have to meet with a CI; voight says to bring some backup. you want in?”

hailey stands so fast; she nearly topples over her chair. “oh god, yes,” the reply flies out of her mouth nearly as quickly and vanessa knits her eyebrows together. “i mean, yeah, of course i’ll go with you.”

hailey spares a glance over at Jay and is slightly pleased to see him smirking; maybe he isn’t as far gone as she thinks.

* * *

that night, hailey finds herself at molly’s.

she has no idea where erin and jay plan on meeting up, but she prays that it isn’t molly's because she is in desperate need of shots.

the rest of her team isn’t here either. kim and adam went to dinner (honestly, can those two just get together already?) and surprisingly, vanessa is out with kevin, but she has no idea where. so, hailey sits at the bar by her lonesome, but it’s fine.

she downs another shot of tequila.

she’s fine.

her pity-party is interrupted when a stool is dragged next to her. she looks up to see the other halstead, nursing a beer and a smile. “hey herrmann, can we get another round please?” he asks the older fireman.

“you got it,” he replies and then glances at hailey, “i'll throw in another round of shots on the house. looks like this one needs it,” he drops his right eyelid in a wink.

hailey opens her mouth to object because this is absolutely mortifying but nothing comes out. “make it a double, please,” she says instead.

“oh no, what did he do now?” will asks in jest, gladly accepting the drinks herrmann is laying out for them.

hailey smirks. “who?” she asks innocently.

“you may be a detective, but i can also see through your bullshit,” will sasses with a raised eyebrow. “now tell me, what stupid thing did my brother do today?”

hailey laughs; she doesn’t usually spend much time with will, at least not without jay around. but it’s nice; his company is nice. “he didn’t do anything,” she replies, and she isn’t lying. but somehow it feels like she is.

“so, what’s the reason for all this?” he motions to the shots, which only spurs her to take another.

her face scrunches at the burn of the amber liquid and she turns to look at him. his face is blank, save for a little curiosity. but he’s there and he’s ready to listen and it just comes pouring out.

“erin is in town.”

will's jaw instantly drops, but he recovers quickly. he takes a hold of his own shot glass and holds it out to her, waiting. she brings their glasses together in cheers and throws it back.

“how did jay react to that?”

hailey nearly laughs. “like a robot. honestly, do you bottle up your emotions as much as he does?”

“i'm proud to say that no, i do not,” he chuckles. “i'm much more emotional than jay—don’t tell him that, though.”

hailey laughs and she’s so glad for the distraction. “he didn’t really say anything, and i couldn’t read him. so, i got nervous and maybe said some things i shouldn’t have.”

will raises an eyebrow in curiosity. “what kind of things?”

“like maybe she’s pregnant,” his eyes widen and he bursts out in laughter, “and then i just had to mention that maybe she wants to get back together,” she rolls her eyes, “honestly, he’s going to fold like a pancake as soon as he sees her.”

will is still laughing. “i'm not sure where the pancake reference is coming from, but i can assure you jay doesn’t want anything more than closure and a beer.”

“how do you know that?” hailey asks, pouting. then she straightens up and drops her facial expression because she’s a goddamn adult for fuck sakes.

“you know jay, but i know him better,” will explains, “he was devastated when she left. but that’s just it; she left. and she had no intention of coming back. he’s dumb and reckless sometimes, but he wouldn’t put himself through that again.”

“oh,” hailey exhales softly, suddenly feeling ridiculous for her overreaction. “i guess that makes sense.”

will smirks. “he's not the best with change. he had to adapt to her leaving and he can’t live in fear knowing that she might have to leave again; she didn’t even say goodbye.”

hailey remembers the first months of their partnership. he was stubborn and dark, and it took her a while to get through to him; it seems stupid but the first morning he brought her a coffee without having to ask her order beforehand, that’s when she knew things were going to change. and they did; look at them now.

“plus, why would he get back together with erin when he’s clearly in love with you?”

hailey's head whips around to stare at will with wide, worried eyes. but his gaze is locked on molly’s front doors where jay has just entered; he’s looking around, wondering if anyone from his unit is here (since no one replied to his texts in the group chat), but then he spots his brother’s wild red hair and his blonde partner beside him.

“i guess this is my cue to leave,” will says quickly as he rushes to finish the last of his beer.

hailey latches onto his arm, panicking. “what?” she hisses. “no, you can’t leave! not after saying something like that!”

“oh, do you hear that?” will says, standing and grabbing his coat. “i’m being paged. sorry hailey, but i have to go save lives,” he replies, smirking because clearly he is not being paged and hailey is livid.

hailey narrows her eyes. “okay halstead, play the doctor card; i see how it is,” she responds, but sharply adds, “i’ll remember this.”

“you’re a sassy woman, hailey,” will smiles, “i see why my brother likes you so much.”

this time he makes sure jay hears it as well and thoroughly enjoys watching hailey drown her embarrassment in her beer, while jay looks on, confused as hell.

“hey jay! sorry, i gotta run. busy doing doctor stuff, you know?”

will doesn’t wait for a response and he’s out the door before jay can even blink.

“he's such a loser,” jay snorts and vacates will's old spot. he orders a beer for himself and another one for hailey and herrmann obliges, holding back his smirk. “am i missing something here?”

hailey shakes her head quickly. “no, of course not,” she replies, “how’s erin?”

“she's good,” he replies casually. hailey continues to look at him and when he notices, she motions for him to go on. “oh, i don’t know. she's fine, i guess. came down for a case and wanted to check in. didn't call the rest of the unit because she’s leaving tomorrow and didn’t want to make a big deal.”

his answers are so vague and she’s getting frustrated.

“jay, she’s your ex-girlfriend. that's all?” hailey prods; she can’t help herself.

his green eyes zero in on her expression, wondering where this persistence is coming from. to some degree, he knows because he caught her nervousness earlier in the break room and clearly, there’s a reason for it. “yeah, that’s all. we had one drink, i gave her the rundown on all the changes within Intelligence and she told me a bit about her new job.”

“that's it?” hailey asks with hopeful eyes.

jay mirrors her expression but with confused eyes. “that's it.”

hailey visibly deflates and she takes another swig of her beer with elated ease. her actions cause a smirk to appear on jay's face, as he leans his body forward. “hailey,” she hums in response, “is there anything you’d like to tell me?”

the ease that hailey was feeling for two seconds is suddenly gone and replaced with stone cold anxiety.

“because earlier today, you were chatting my ear off about erin-related topics and you were clearly nervous. now that i’m telling you absolutely nothing happened, you’re looking very relieved. what am i missing?”

jay's eyes bore into hers and he can clearly see she’s nervous once again, but she tries to keep her expressions in check. “i'm just glad you’re okay. i didn’t want you to get hurt again.”

jay is 99% sure she’s lying, but it’s a damn good lie.

“and that’s all?” he asks with a raised eyebrow.

hailey snaps out of her trance and punches his shoulder; that certainly snaps him out as well as he groans. “i care about you, jay! i’m just looking out.”

he narrows his eyes at her, because she’s good, but she can’t lie to him.

“i know there’s more,” he says simply, standing and grabbing a few bills from his wallet. “and we’ll have that conversation someday.”

he grabs his jacket.

“jay,” hailey breathes and for a moment, she thinks she can do this; it’s time.

but she doesn’t say anything.

he sends her a soft smile. “goodnight, hailey.”

he leans down to press a kiss to her cheek. she inhales sharply.

she watches him walk out the door and can’t find it in herself to chase after him.

she lets him go.

**Author's Note:**

> okayyyy so, i had a request to write erin and this isn't quite what i was thinking but it's what i ended up with lmao. so the plan is to write another fic eventually and actually include erin in it... so if yall have any idea on what you want to go down.. LET ME KNOW!
> 
> also, i love goofy hailey.. she's so in love
> 
> ALSO, sorry about the ending but idk i was feeling it
> 
> and of course, i'd like to mention, no hate AT ALL to erin lindsay. i loved her character and i loved her when she was with jay, but personally i don't think they're right for each other.
> 
> anyway, hope you guys enjoyed!
> 
> also be sure to follow me on tumblr; ruzek-halstead!!


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